Chesterton vacation rentals

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Discover a selection of 26 homes and other vacation rentals in Chesterton that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll have the amenities you expect and more, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Tranquil Chesterton will entice you

The riverfront, beaches and lake are a perfect backdrop to your vacation home in Chesterton. Travelers to this relaxing city praise the coffeehouses, bird watching and shopping. Take in top local attractions like Indiana Dunes National Park and Lake Michigan. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chesterton

Do you want to find attractions to visit in the city? Venture out of your vacation home and experience everything that Chesterton has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Washington Park Zoo (11.6 mi / 18.6 km)
  • Deep River Water Park (12.9 mi / 20.8 km)
  • Albanese Candy Factory (14.4 mi / 23.2 km)
  • Shady Creek Winery (14.5 mi / 23.3 km)
  • Oasis Splash Pad (11.6 mi / 18.7 km)
  • The Course at Aberdeen (11.9 mi / 19.1 km)

Exploring the natural landscape of Chesterton

Travelers enjoy Chesterton for its beaches and lakeside setting. Whether you're an outdoor enthusiast or just want to take in the scenery, Chesterton is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Indiana Dunes National Park (2.7 mi / 4.3 km)
  • Indiana Dunes Visitor Center (1.7 mi / 2.7 km)
  • Indiana Dunes State Park (3.2 mi / 5.2 km)
  • Lake View Beach (6.4 mi / 10.3 km)
  • Ogden Dunes Beach (6.9 mi / 11.1 km)
  • Beverly Shores Beach (7.2 mi / 11.6 km)

Seasonal weather in Chesterton

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 70°F.

Transportation to and around Chesterton

The nearest airport is in Chicago Midway Airport (MDW), located 37 mi (59.6 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chesterton?

According to our research, houses are the most sought-after type of vacation property in Chesterton. But that goes without saying, everyone's idea of an epic trip isn't the same. Vrbo has vacation homes of all sizes, shapes and budgets, so you're bound to find the perfect fit for you.

How much does it cost to rent a vacation rental in Chesterton?

Length of stay, property type and season are some of the things that can affect the price of a vacation home. Simply click on your dates of travel to find your ideal match. From comfy cottages to expansive villas, all Vrbo vacation rentals provide amazing value.

How much does it cost to rent a beach house in Chesterton?

Prices for beach houses in Chesterton may vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to view your vacation rental options and prices. From there you can use our filter tool to tailor your search by ratings, nearby activities, amenities and more.

Are there pet-friendly vacation rentals in Chesterton?

Yes. You'll have a choice of 17 vacation homes that roll out the welcome mat in Chesterton on Vrbo. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where Spot can join in the fun.

What are popular rental amenities in Chesterton?

Some of the most popular rental amenities people are searching for in Chesterton include a barbecue grill, nearby museums and a garden. Whether you're hitting the road with family, buddies or even pets, Vrbo vacation homes come with the best amenities for hanging out with the people you love.

Are there large group vacation rentals in Chesterton?

With 11 Chesterton vacation homes that can host a group of five or more people, you can bring a few extra pals or family members along. Whether you're planning an informal get-together or a birthday party, Vrbo will help you find a comfy space for the occasion.

Are there vacation rentals in Chesterton that welcome kids?

Gather your whole family for a fun-packed adventure in Chesterton at one of our 17 family-friendly vacation properties. Many of these stays come with amenities that are ideally suited to getaways with children, including kitchens, living rooms and entertainment units. Simply check the "Properties good for families" filter box and pick out your favorite.

What are the top attractions for families in Chesterton?

You'll find loads of exciting things to do and see with the family in Chesterton, including:

  • Lake View Beach
  • Portage Lakefront Beach
  • Dune Acres Beach

Are there one-bedroom vacation rentals in Chesterton?

Chesterton has two one-bedroom rentals available. Often located in desirable areas due to their smaller size, a one-bedroom vacation rental is great if you're traveling with your partner or a buddy. And with home comforts such as full kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this awesome destination.

Can I find two-bedroom vacation rentals in Chesterton?

You can select from five two-bedroom vacation rentals in Chesterton. Settle the kids into the second room or fill it with a couple of your best friends. There's space for whoever's lucky enough to be coming along for the ride.

Are there vacation rentals with WiFi in Chesterton?

There are seven vacation rentals with WiFi in Chesterton. If you want to disconnect from the world on your break, but still need to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Chesterton?

Chesterton has 17 vacation rentals where you can chill out in air-conditioned comfort. To book a property on Vrbo that comes with this amenity, enter your dates of travel and use the handy filters to select the "air conditioning" box.

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